Hydrochloric Acid → 1-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole

HRID 612844

反応式

HRID 612844 の反応式
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][CH3:11].C([O-])(=O)C.[Na+].S(O)(=O)(=O)C.[CH:23]1([NH:29][NH2:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.Cl>C1(C)C=CC=CC=1>[CH:23]1([N:29]2[C:2]3[C:3](=[CH:4][CH:5]=[C:6]([F:8])[CH:7]=3)[C:9]([CH2:10][CH3:11])=[N:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1235862',4'-DifluoropropiophenoneHCID 517045Sodium AcetateHCID 22009940Cyclohexylhydrazine mesylate

生成物 1

HCID 98596991-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole収率 98%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 1-(2,4-difluoro-phenyl)-propan-1-one (21.29 g, 125.1 mmol) in toluene (120 mL) was added sodium acetate (26.75 g, 326.1 mmol) and cyclohexylhydrazine mesylate (34.0 g, 163 mmol). The reaction mixture was heated to reflux in a Dean-Stark apparatus for 12 hours. The reaction was cooled to room temperature and poured into 1 N hydrochloric acid (100 mL). The toluene layer was separated and washed with water (75 mL) and brine (75 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to yield 30.07 g of 1-cyclohexyl-3-ethyl-6-fluoro-1H-indazole (98% yield). 1H NMR (400 MHz, CDCl3) d 1.33 (t, 3, J=7.7), 1.35-1.44 (m, 2), 1.47-1.96 (m, 8), 2.93 (q, 2, J=7.7), 4.14-4.22 (m, 1), 6.81 (dt, 1, J=8.9, 2.1), 6.99 (dd, 1, J=9.8, 2.1), 7.40 (ddd, 1, J=8.7, 5.2, 0.4). 13C NMR (100 MHz, CDCl3) d 13.97, 20.53, 25.37, 25.84, 32.32, 58.18, 94.77 (d, J=27.4), 109.11 (d, J=26.0), 119.38, 121.75 (d, J=11.5), 139.89 (d, J=13.0), 146.61, 161.95 (d, J=242).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux in a Dean-Stark apparatus for 12 hours
  3. customThe toluene layer was separated
  4. washwashed with water (75 mL) and brine (75 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-db61696e0bf84900b117dc58b2730888
出典データセット
uspto-grants-1999_12
特許番号
US06005118

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